Drugstore Cowboy
Set in the director's adopted town of Portland and the Pacific Northwest, Drugstore Cowboy conferred a career-defining role on Matt Dillon as Bob, a shameless dope fiend more interested in scoring drugs than cosying up to his sexually frustrated wife (Kelly Lynch).
When Bob and his on-the-lam crew (James LeGros and Heather Graham) check in to a motel hosting a sheriffs' convention, he decides it might be time to turn over a new leaf.
Key Van Sant motifs - dryly self-aware yet spiritually exiled first-person narrators, time lapse photography, trippy point-of-view shots, Super 8 flashbacks - are all on show in the director's break-out indie hit.
A brilliantly caustic William Burroughs appears as a philosophising priest with typically unsanctioned views on the role of narcotics in society.